Transamerica stars Felicity Huffman as a pre-operative male-to-female transsexual, Bree, who finds herself coming face to face with a son she never knew she had, on the eve of her sexual reassignment surgery.

Bree is working two jobs and living as a “genetic girl” in a poor Los Angeles neighbourhood. She receives a phone call for Stanley (her pre-trans male name) from a jail in New York City, where her son has landed. Bree's therapist Margaret (Elizabeth Peña) requires her to fully reconcile her past life as Stanley before she will sign off on Bree's surgery; this set-up triggers a trip to New York and the picaresque road trip back to Los Angeles with the her son Toby (Kevin Zegers) who is a street-hustling prostitute.

There is one small catch — Bree withholds her real identity, or identities, from Toby. When she arrives in New York to have Toby released into her custody, she allows herself to be identified as a Christian missionary from the “Church of the Potential Father.” This initial lie only leads to more lies. The fearful yet hopefully “passing” pre-op seems incapable of telling the truth at first (and conversations with her therapist indicate this is an ongoing problem for Bree). The potentially drug-addicted, street-hustling teenaged traveling companion picks up on this right away. Short on-the-road side stories offer glimpses into the realities of living and surviving as a transgendered person in America.

As Bree slowly opens up to Toby (and in some ways herself), the plot unfolds along two parallel tracks, both typical of buddy movies. While she and Toby wrestle with each other, learning to trust in spite of betrayals and setbacks of that trust, they grow to know and love each other. Through it all, Bree discovers that she takes to motherly nurturing like a duck to water.

Many surprises await Bree and Toby on the road. Early on, they make the mistake of picking up a young blond hippie hitchhiker (Grant Monohon), who works his charisma on them both, to tragic effect. Shortly after, Bree is outed in Kentucky during an early overnight stop along the road. They are to spend the night at the home of a “fellow missionary friend,” who happens to be holding a support meeting for local transpeople, none of whom realize Bree has not come out to her young son. The camera's point of view is with Bree, allowing the viewer to experience being “outed” with her.

Arriving at Bree's childhood home in suburban Arizona (Bree's current poverty is a striking contrast to the suntanned exuberant lifestyle of her parents), the viewer is treated to the standard litany of dysfunctional family jokes, but with a transgendered twist. Fionnula Flanagan plays Stanley's mother Elizabeth, Burt Young his father Murray, and Carrie Preston his rivalrous sister Sidney. As grandparents, Elizabeth and Murray try to gain custody of their newly discovered grandson. Everyone is forced, finally, to start dealing with some not so jocular, long-standing, long unresolved realities. In the middle of the shenanigans comes a touch of grace for Bree, the unexpected mutual romantic interest with Calvin Manygoats (Graham Greene).

Transamerica stands alongside Sideways in the sudden revitalization of the American road-trip picture. Like the character Bree Osborne, it's not exactly drama, and not exactly comedy, but definitely some of both. The delightful balancing of whimsy and deadly seriousness, light-hearted humor and cutting parody, all underscore the transgender message.